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Take a day trip to Assisi and Cortona and discover these charming hilltop towns alongside a guide. Departing from Florence, travel first to Assisi, where you’ll visit the Convent of Santa Chiara, the Basilica of San Francesco, and hear about the life of St. Francis of Assisi. Pause for a peek inside Santa Maria degli Angeli church, believed to be a favorite spot of St. Francis. Then head to Cortona for some time to explore independently before returning to Florence.

Visit two of Tuscany’s spectacular hilltop towns on a full-day, small-group tour from Rome to Cortona and Arezzo, and discover historic architecture, artwork, and neighborhoods with views of the Tuscan countryside. Take in film locations from ‘Under the Tuscan Sun’ and ‘Life is Beautiful’ as you spend the day with a knowledgeable guide, exploring Tuscany at its most picturesque. This full-day tour includes pickup at centrally-located Rome hotels, and is limited to 15 people for a personalized experience.

Spend a day in the Tuscan countryside on this private day trip from Siena. With your own driver, you'll travel first to Arezzo, a town that's home to esteemed religious works by Cimabue and Piero della Francesca. After visiting the town, cathedral, and a restaurant for lunch, you'll head through the scenic Val di Chiana to reach the Etruscan city of Cortona. Soak up the views from the Basilica of Santa Margherita, then return to Siena via a winery near Montepulciano to taste the local wine.

Sip some of Italy's best vino with a private full-day wine tour in Montalcino from Cortona. Visit two wineries to taste the famous Brunello wines produced in this part of Tuscany. Learn what makes Brunello so special from sommeliers and wine experts. Sample a selection of Tuscan meats and cheeses with the wine. Have lunch in a winery and visit either Montalcino or the Sant'Antimo Abbey before the end of the tour.